Vacation rentals in Dorset Hill

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Top-rated vacation rentals in Dorset Hill

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Top guest favorite
The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.
Cabin in Londonderry
4.94 out of 5 average rating, 371 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest favorite
A cozy bedroom features a metal bed frame adorned with a colorful quilt. Soft pillows are arranged at the head of the bed, and a bedside lamp provides gentle illumination. An angled ceiling creates an intimate atmosphere, complemented by a framed landscape picture on the wall.
Guesthouse in Manchester
4.76 out of 5 average rating, 281 reviews

Romantic Barn Guesthouse in Village Center

Keep it simple at our peaceful and centrally-located hideaway. This rustic and cozy two-story barn guesthouse with fireplace is located on four acres of a 1768 historic homestead right in Manchester Center. Enjoy the pond and mountain views from the bedroom and living room windows; the guesthouse faces a peaceful meadow and wildlife pond which abuts 70 acres of preserved land with hiking trails, yet it's also just steps from Main Street and all of the dining and shopping of Manchester Village.

Guest favorite
A comfortable living area features a sectional sofa adorned with soft pillows and a wooden coffee table. Natural light floods in through a large window, highlighting the wooden wall paneling. A decorative rug rests under the table, adding warmth to the space.
Home in Dorset
4.9 out of 5 average rating, 101 reviews

Mountain View Getaway

Escape to our cozy, inviting home nestled on the side of a mountain in East Dorset, VT. This peaceful getaway features 2 spacious bedrooms and 1.5 modern bathrooms, perfect for families or couples. Enjoy a fully equipped kitchen, a relaxing living area, and a beautiful backyard with a deck for outdoor dining. Explore nearby hiking trails, skiing, swimming, local attractions, or simply relax in nature's beauty. Easy check-in and check-out. No smoking Well trained pets only No large parties

Top guest favorite
The entrance of the Bonnet St Barn features a deep red exterior with a sloping roof and an overhang. A small chair is positioned beside the door, framed by lush greenery and blooming flowers, enhancing the welcoming entryway.
Apartment in Manchester
4.99 out of 5 average rating, 104 reviews

Bonnet St Barn

Keep it simple at the peaceful, cozy and centrally-located Bonnet St Barn. Conveniently located steps from Manchester’s landmark 'Northshire Bookstore', restaurants and delightful shopping. The apartment is on the main floor of the two-story barn and features a king-size bed, a smaller second bedroom with a twin bed, AC, high speed WiFi, TV and a full kitchen for relaxing mealtimes. Less than 30-minute drive to Bromley & Stratton ski areas. Enjoy the Green Mountains of southern Vermont!

Top guest favorite
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 280 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Top guest favorite
An open living space is depicted, featuring a kitchen area with a stove and a kettle. A cozy sofa is positioned nearby, with large windows allowing natural light to fill the room. A staircase leads to a sleeping loft, visible above, with a unique railing design.
Guest suite in Manchester
4.91 out of 5 average rating, 153 reviews

Bright Manchester Studio with Sleeping Loft

Our studio apartment with sleeping loft is great for two adults or a couple with children. Located on a quiet country road great for taking long walks. There is a queen bed in the loft and a pull out queen sofa in the living area. Bright with high ceilings and all new furnishings. We are less than three miles from town, 20 minutes to Bromley and 25 minutes to Stratton. Close to hiking, biking, fishing, great restaurants and shopping. Please note;Owners lives on premise in main house.

Top guest favorite
The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.
Apartment in Middletown Springs
4.89 out of 5 average rating, 276 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Top guest favorite
A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.
Home in Winhall
4.99 out of 5 average rating, 134 reviews

3BR 2BA Stratton Condo w/ Fireplace & Forest Views

Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Top guest favorite
The green barn structure features a deck with white railings, providing access through double doors. Lush grass surrounds the building, with trees framing the background. A gradient sky at sunset displays soft hues of pink and orange, creating a serene outdoor setting.
Barn in Manchester
4.99 out of 5 average rating, 292 reviews

Big Green Barn - Manchester Village Vermont

Unique Vermont Barn Experience! 1880s restored barn on 2 acres in Manchester Village across from Southern Vermont Arts Center. Converted to a photo studio in 2004 when we moved from NY; spacious, comfortable, solar-powered, approx. 1 mile to Main St. (town roads, no sidewalk), close to shopping, restaurants, golf, hiking, skiing, etc. Beautiful views, Mount Equinox front, the Green Mountains back. No pets. Not suitable for children under 12. (License number MRT-10126712)

Top guest favorite
Cabin in Winhall
4.96 out of 5 average rating, 368 reviews

Dog Friendly A-Frame Retreat near Hiking, Skiing

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Top guest favorite
Home in Clarendon
4.95 out of 5 average rating, 317 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Top guest favorite
The exterior of a two-story house is visible, featuring a sloped roof and white siding. Lush green bushes frame the front yard, where a small decorative archway and white picket fence add charm. Surrounding trees provide a natural backdrop for the property.
Apartment in Manchester
4.99 out of 5 average rating, 301 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio.

Popular amenities for Dorset Hill vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Dorset
  6. Dorset Hill